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SML2040

Sigma-Aldrich

Liarozole dihydrochloride

≥98% (HPLC)

Synonym(s):

5-[(3-Chlorophenyl)(1H-imidazol-1-yl)methyl]-1H-benzimidazole, 6-[(3-Chlorophenyl)(1H-imidazol-1-yl)methyl]-1H-benzimidazole dihydrochloride, R 75251 dihydrochloride, R-75251 dihydrochloride, R75251 dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C17H13ClN4 · 2HCl
CAS Number:
1883548-96-6
Molecular Weight:
381.69
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 2 mg/mL, clear

storage temp.

room temp

SMILES string

ClC1=CC(C(C2=CC=C3N=CNC3=C2)N4C=CN=C4)=CC=C1

Biochem/physiol Actions

Liarozole (R 75251, R75,251) is an orally active benzimidazole-based retinoic acid (RA) metabolism blocking agent (RAMBA) that targets multiple P450 enzymes, including aromatase (CYP19), 17-hydroxylase/17,20-lyase (CYP17A1), 11-hydroxylase (CYP11B1), and RA 4-hydroxylase (CYP26). Liarozole is more effective than ketoconazole in vivo (plasma RA enhancement = 2.5 ng/mL vs. 1.3 ng/mL 2 hr after respective oral dosage of 40 mg/kg in rats) and, in contrast to ketoconazole, Liarozole does not significantly affect circulating adrenal androgen levels. Liarozole is shown to effectively suppress androgen-dependent tumor expansion of R3327G Dunning prostate adenocarcinoma xenografts in rats (by 66% and 81% with 80 and 120 mg/kg/day p.o., respectively) independent of its androgen biosynthesis inhibition.
Orally active retinoic acid (RA) metabolism blocking agent (RAMBA) with higher in vivo efficay than ketoconazole.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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R Van Ginckel et al.
The Prostate, 16(4), 313-323 (1990-01-01)
The antitumoral activity of a novel imidazole derivative, R 75,251, has been studied in the androgen-dependent R3327G Dunning prostate adenocarcinoma grafted subcutaneously in syngeneic rats. Dietary application resulting approximately in dose levels of 80, 120, and 160 mg/kg reduced tumor
J P Van Wauwe et al.
The Journal of pharmacology and experimental therapeutics, 252(1), 365-369 (1990-01-01)
This study examines the effects of ketoconazole, R 75 251 and some other cytochrome P-450 inhibitors on the in vivo metabolism of all-trans-retinoic acid (RA) in normal rats. Oral treatment with ketoconazole or R 75 251 (40 mg/kg, -1 hr)
J Bruynseels et al.
The Prostate, 16(4), 345-357 (1990-01-01)
R 75251, a new imidazole derivative, inhibited the conversion of androgens to estrogens, of progestins to androstenedione and testosterone, and of 11-deoxycorticosterone to corticosterone in human placenta microsomes, subcellular fraction of rat testis, bovine adrenocortical mitochondria, in cultured rat granulosa

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